"A 69-year-old white man with a medical history of left-sided cluster headaches presented for evaluation of dermatochalasis. The left upper eyelid demonstrated red-pink, blanchable macules that coalesced in a patch. The lesion appeared after an episode of a cluster headache. Histopathologic evaluation demonstrated aggregates of telangiectatic blood vessels in the papillary dermis consistent with the diagnosis of an acquired port wine stain. The authors report, to their knowledge, the first description of an acquired port wine stain associated with cluster headaches."